3,4-Dichlorobenzeneboronic acid → 4-chloro-2-(3,4-dichlorophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridine

HRID 1508828Notes

Reaction equation

HRID 1508828 reaction equation
Cl[C:2]1[N:7]=[C:6]2[CH2:8][CH2:9][CH2:10][C:5]2=[C:4]([Cl:11])[CH:3]=1.[Cl:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][C:18]=1[Cl:19]>>[Cl:11][C:4]1[CH:3]=[C:2]([C:16]2[CH:15]=[CH:14][C:13]([Cl:12])=[C:18]([Cl:19])[CH:17]=2)[N:7]=[C:6]2[CH2:8][CH2:9][CH2:10][C:5]=12

Participants

3

Reactant 2

HCID 27343303,4-Dichlorobenzeneboronic acidHCID 122148172,4-Dichloro-6,7-dihydro-5H-cyclopenta[b]pyridine

Product 1

HCID 903386694-chloro-2-(3,4-dichlorophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridineYield 94%

Procedure

Following General Procedure F, 2,4-dichloro-6,7-dihydro-5H-cyclopenta[b]pyridine (0.150 g, 0.80 mmol) was reacted with (3,4-dichlorophenyl)boronic acid (0.198 g, 1.04 mmol) to afford the title compound (0.141 g, 94%). MW=298.59. 1H NMR (CD3OD, 300 MHz) δ 8.16 (d, J=2.1 Hz, 1H), 7.90-7.84 (m, 1H), 7.69 (s, 1H), 7.61 (d, J=8.5 Hz, 1H), 3.12 (t, J=7.6 Hz, 2H), 3.05 (t, J=7.6 Hz, 2H), 2.21 (quin, J=7.6 Hz, 2H); APCI MS m/z 297 [M+H]+.

Sources & evidence

ORD record
ord-c6b9a9d13daa48feb8e45be00a196d5f
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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